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. 2024 Dec 3;16(2):962–969. doi: 10.1039/d4sc04997g

Table 1. Optimization of coupling of amide 1a and silyl enol ether 2aa,b.

graphic file with name d4sc04997g-u1.jpg
Entry Solvent Photocatalyst Conc. [M] Assay yield (%)
1 DMF fac-Ir(ppy)3 0.1 40
2 DMSO fac-Ir(ppy)3 0.1 68
3 CH3CN fac-Ir(ppy)3 0.1 27
4 DCM fac-Ir(ppy)3 0.1 0
5 DCE fac-Ir(ppy)3 0.1 12
6 THF fac-Ir(ppy)3 0.1 18
7 PhCl fac-Ir(ppy)3 0.1 20
8 PhCF3 fac-Ir(ppy)3 0.1 Trace
9 EtOH fac-Ir(ppy)3 0.1 0
10 DMSO 4CzIPN 0.1 13
11 DMSO [Ir(dtbbpy)(ppy)2][PF6] 0.1 31
12 DMSO [Ir(ppy)2(bpy)]PF6 0.1 26
13 DMSO Eosin Y 0.1 18
14c DMSO fac-Ir(ppy)3 0.1 94 (90)d
15c DMSO fac-Ir(ppy)3 0.2 86
16c DMSO fac-Ir(ppy)3 0.05 77
17c DMSO — 0.1 0
18e DMSO fac-Ir(ppy)3 0.1 0
a

Reaction conditions: 1a (0.1 mmol, 1.0 equiv.), 2a (0.15 mmol, 1.5 equiv.), PC (2 mol%), rt, 6 h.

b

Assay yields determined by 1H NMR spectroscopy of the crude reaction mixtures using CH2Br2 as an internal standard.

c

1.5 : 1 ratio of 1a to 2a.

d

Isolated yield after chromatographic purification.

e

Without blue LEDs.